Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 17, Pages 2869-2874Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000659
Keywords
chromans; 3,4-dihydrocoumarins; hemiacetalization; Michael addition; organocatalysis
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Funding
- Deutsche Forschungsgemeinschaft
- Fonds der Chemischen Industrie
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The organocatalytic domino Michael/hemiacetalization reaction between various aldehydes and ortho-nitrovinylphenols has been developed. Under the catalysis of diphenyl prolinol trimethylsilyl ether, cis-3,4-disubstituted chromanols are obtained in high to excellent yields (81-98%) and stereoselectivities (dr: 86:14 to >99:1, ee 96 to > 99%). The corresponding disubstituted chromans are available by dehydroxylation of the domino products in good to excellent yields (58-95%). Furthermore, oxidation of the domino products with pyridinium chlorochromate provided 3,4-dihydrocoumarins in good yields (65-83%) without any epimerization.
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